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...I've been browsing all over, and it seems that most of the new models are too bright and/or ugly to ever be seen in a casual setting. The closest I could find were possibly these lunarglides or these pegasus'.

I regularly spend $100 on running shoes and when they reach 400-500 miles, I retire them. If I could start getting some ones that work with jeans, I could double the life of the shoe....what do you guys think?

If you're using them for running, you should choose for your biomechanic needs first. Shoes are considered "done" at the point you're mentioning. In my opinion, they're not good for walking either after this point.

That being said, nike frees are pretty popular in street fashion right now

I can see your point.
Would you agree, though, that a retired running shoe would be better for your feet than most of what people wear in the summer, such as flimsy boat shoes or ancient 10 dollar flip flops?

It depends on what you think "better" is. When your running shoes are done, the cushioning is pretty much shot. This is why you can't run in them anymore. A "boat shoe" might be missing other features the running shoe has, like stability (you're looking at neutral shoes so perhaps this is irrelevant) but more cushioning. Some flip flops have rather excellent arch support.

If it were me I'd invest in some walking shoes designed to last long term (like birkenstock sandals). This may be a better investment than compromising your running shoes/limiting your options just so you can walk in them after

A lot of fashionable types are wearing Flyknits with everything from jeans to suits. Looks pretty sweet. But you shouldn't buy your running shoe based on how they look, you should buy them based on how they feel.

In my case, though, I've spent the last 15 years or so choosing something decent from nike or ascics and I've never had any shoe issues whatsoever. I am fairly biomechanically efficient, so have a good variety to choose from. (For other runners, maybe not so much.)

I'm a big fan of the NB 890s. They usually come in lots of colors. The current version has a plaid and an argyle pattern...pretty dressy. Plus they have plain colors too if you're into that. A great shoe.

If you're a neutral runner with normal-narrow foot these are good. Moderate cushioning (not super plush like Asics Cumulus...if you're familiar with those). They do have a little less width in the toe box--which I don't prefer, but I run so much I don't even care--as long as they keep me injury free.

Pretty good idea actually. I pick the shoes that feel the best, then pick the brightest color generally for visibility purposes. Might switch to obnoxious shirts/hat combo and start saving money on day to day shoes.

I love New Balance - well-made, inexpensive, and produced in a wide range of sizes. But I don't suggest using your actual running shoes for anything else between runs - let those poor things breathe. And once they're shot for running, they aren't really suitable for walking very far either.

Some ppl actually run barefoot. They say gel shoes spoil feet muscles.
I don't think you should run in jeans, get some sport shorts or swarpants instead.
And don't forget to stretch before and after running, at least for few minutes. Just to avoid injuring yourself.